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PubMed2006

Isolation and structure elucidation of cytotoxic polyacetylenes and polyenes from Echinacea pallida.

Bioassay-guided fractionation of n-hexane extracts of Echinacea pallida (Asteraceae) roots led to the isolation and structure elucidation of two polyacetylenes (1, 3) and three polyenes (2, 4, 5). Two are known hydroxylated compounds, namely 8-hydroxy-pentadeca-(9E)-ene-11,13-diyn-2-one (1) and 8-hydroxy-pentadeca-(9E,13Z)-dien-11-yn-2-one (2). Two dicarbonylic constituents, namely pentadeca-(9E)-ene-11,13-diyne-2,8-dione (3) and pentadeca-(9E,13Z)-dien-11-yne-2,8-dione (4), were isolated and characterized for the first time. Furthermore, the structure elucidation of pentadeca-(8Z,13Z)-dien-11-yn-2-one (5) is described. The structure of the compounds isolated was determined on the basis of UV, IR, NMR (including 1D and 2D NMR experiments, such as 1H-1H gCOSY, gHSQC-DEPT, gHMBC, gNOESY) and MS spectroscopic data. The cytotoxic activity of the isolated constituents against MIA PaCa-2 human pancreatic adenocarcinoma cells was evaluated in the concentration range 1-100 microg/ml. Results show that the hydroxylated compounds (1, 2) have low cytotoxicity, while the more hydrophobic polyacetylenes (3) and polyenes (4, 5) displayed moderate activity.

Acetylene↗
PubMed2006

Modulatory effects of Echinacea purpurea extracts on human dendritic cells: a cell- and gene-based study.

Echinacea spp. are popularly used as an herbal medicine or food supplement for enhancing the immune system. This study shows that plant extracts from root [R] and stem plus leaf [S+L] tissues of E. purpurea exhibit opposite (enhancing vs inhibitory) modulatory effects on the expression of the CD83 marker in human dendritic cells (DCs), which are known as professional antigen-presenting cells. We developed a function-targeted DNA microarray system to characterize the effects of phytocompounds on human DCs. Down-regulation of mRNA expression of specific chemokines (e.g., CCL3 and CCL8) and their receptors (e.g., CCR1 and CCR9) was observed in [S+L]-treated DCs. Other chemokines and regulatory molecules (e.g., CCL4 and CCL2) involved in the c-Jun pathway were found to be up-regulated in [R]-treated DCs. This study, for the first time, demonstrates that E. purpurea extracts can modulate DC differentiation and expression of specific immune-related genes in DCs.

Antigens, CD↗
PubMed2000

Characterization of an arabinogalactan-protein isolated from pressed juice of Echinacea purpurea by precipitation with the beta-glucosyl Yariv reagent.

An arabinogalactan-protein (AGP) from pressed juice of Echinacea purpurea herb was isolated from a high molecular weight fraction by precipitation with the beta-glucosyl Yariv reagent, followed by gel-permeation chromatography. It revealed characteristic features of other AGPs: i.e., a high amount of polysaccharide (83%) with a ratio of galactose to arabinose of 1.8:1, some uronic acids (4-5%), and a low protein content (7%) with high levels of serine, alanine and hydroxyproline. The molecular weight was estimated to be 1.2 x 10(6) Da. Linkage and 13C NMR analyses showed that the AGP is composed of a highly branched core polysaccharide of 3-, 6-, and 3,6-linked Galp residues with terminal Araf, GlcAp and terminal units of Araf-(1-->5)-Araf-(1-->. Partial acid hydrolysis resulted in loss of Araf residues at the periphery of the molecule. Complete loss of reactivity toward the beta-glucosyl Yariv antigen was then noticed.

Carbohydrate Conformation↗
PubMed2001

Synthesis of the alpha-L-Araf-(1-->2)-beta-D-Galp-(1-->6)-beta-D-Galp-(1-->6)-[alpha-L-Araf-(1-->2)]-beta-D-Galp-(1-->6)-D-Gal hexasaccharide as a possible repeating unit of the cell-cultured exudates of Echinacea purpurea arabinogalactan.

For the characterization of the supposed epitope of an arabinogalactan, isolated from the extract of the cell-cultured Echinacea purpurea, the title hexasaccharide was synthesized. The whole synthetic route was based on the 6-O-(methoxydimethyl)methyl ether (MIP) protecting group strategy. 2-O-Benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta-D-galactopyranosyl-(1-->6)-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose was used to prepare the desired glycosyl donor and glycosyl acceptor both carrying a persistent O-benzyl group at position 2'. Reaction of the digalactose donor and the digalactose acceptor resulted in a beta-(1-->6)-linked galactose-containing tetrasaccharide in which OH-2' and OH-2"' were substituted with benzyl groups. Hydrogenolytic removal of the benzyl groups of the tetragalactose compound gave the diol aglycon which was diarabinosylated in one step to furnish the protected target compound, whose deprotection led to the title hexasaccharide. All of the synthesized compounds were characterized by 1H and 13C NMR spectra, as well as by MALDI-TOF mass-spectrometry measurements.

Cell Culture Techniques↗
PubMed2002

Analysis of phenolic acids by micellar electrokinetic chromatography: application to Echinacea purpurea plant extracts.

A micellar electrokinetic chromatographic (MEKC) method was developed for the separation of ten phenolic acids including cichoric acid and caftaric acids, specific marker phytochemicals of Echinacea purpurea. The MEKC method involved the use of 70 mM sodium deoxycholate (SDC) in 40 mM borate (pH 9.2) buffer and UV detection at 300 nm. The bile acid was used as biosurfactant able to provided a micellar system with different and more selective properties than sodium dodecyl sulfate. The effects of SDC and borate concentration and buffer pH on the analyte resolution were evaluated. The validated method was applied to the determination of cichoric acid and related compounds in E. purpurea root extracts, and in commercial E. purpurea based dried extracts and tablets.

Buffers↗
PubMed2003

Simultaneous analysis of caffeic acid derivatives and alkamides in roots and extracts of Echinacea purpurea by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry.

High-performance liquid chromatography (HPLC) coupled with UV photodiode-array detection and electrospray ionization mass spectrometry was developed for the simultaneous analysis of caffeic acid derivatives and alkamides in the roots and extracts of Echinacea purpurea. Caffeic acid derivatives and alkamides produced very abundant peaks in the total ion current chromatogram during negative and positive cone voltage switching. Cichoric acid and the isomer pair, dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamide, were used as a standard for quantification of caffeic acid derivatives and alkamides in E. purpurea. This novel method surpasses previously published ones in product quality control and providing the HPLC chromatographic fingerprints of biological active components in E. purpurea.

Amides↗
PubMed2001

Predicting quantitative phytochemical markers in single Echinacea plants or clones from their DNA fingerprints.

Amplified restricted fragment length polymorphism (AFLP) data analysis was found to be a statistically significant predictor of phytochemical markers in cultivated Echinacea purpurea germplasm and some related wild species. Over 50 accessions grown under greenhouse conditions were subjected to AFLP analysis and the same assessed for content of tetraene and cichoric acid by high pressure liquid chromatography. The first and second canonical correlation of DNA variables and the phytochemical variables were significant. Individual regressions of cichoric acid and dodeca-2E, 4E, 8Z, 10E/Z-tetraenoic acid isobutyl amide predicted by DNA polymorphism analysis against actual HPLC determined values were nearly linear. Mantel's test showed that there was a weak correlation but a strong association of values of the phytochemical variables and the DNA polymorphism data.

Arachidonic Acids↗
PubMed2001

Methyl jasmonate increases reported alkamides and ketoalkene/ynes in Echinacea pallida (Asteraceae).

Methyl jasmonate (MJ), a naturally-occurring plant cellular signal molecule, was found to induce production of lipophilic secondary metabolites in Echinacea pallida seedlings. Seedling aerial parts were sprayed with 100 ppm MJ, and roots were harvested and extracted 24 h later. Lipophilic root extracts, separated by HPLC, revealed significant increases (P< 0.05) in six alkamides or related ketoalkene/ynes produced by 34 day-old plants and in seven compounds produced by 58 day-old plants.

Acetates↗
PubMed2000

Natural killer cells from aging mice treated with extracts from Echinacea purpurea are quantitatively and functionally rejuvenated.

A growing body of anecdotal evidence in young and adult humans suggests that certain phytochemicals have the capacity to ameliorate tumors and reduce infections, especially those mediated by virus, in vivo. These indications prompted us, therefore, to investigate the potentially immuno-stimulating effect of one such phytocompound, Echinacea purpurea, on natural killer (NK) cells since these cells are active in spontaneous, non-specific immunity against neoplasms and virus-mediated infections. We elected to study aging mice, since, at this stage of life, like humans, the above-mentioned afflictions increase in frequency. We had previously found that neither the cytokine, interleukin-2, nor the pharmacological agent, indomethacin, both potent stimulators of NK cell numbers/function in younger adult mice, was effective in stimulating NK cells in elderly mice. The present study was designed to assess the numbers/production of NK cells in the spleen and bone marrow of aging, normal mice, after in vivo dietary administration of E. purpurea (14 days), or, after injection of thyroxin, a stimulant of NK cell function (10 days). Immunoperoxidase labeling techniques, coupled with hematologic tetrachrome staining were used to identify NK cells in both the spleen (primary site of NK cell function) and the bone marrow (site of NK cell generation). Double immunofluorscence staining, employing propidium iodide, was used to assess NK cell lytic function. Our results revealed that E. purpurea, but not thyroxin, had the capacity to increase NK cell numbers, in aging mice, reflecting increased new NK cell production in their bone marrow generation site, leading to an increase in the absolute numbers of NK cells in the spleen, their primary destiny. The E. purpurea-mediated increase in NK cell numbers was indeed paralleled by an increase in their anti-tumor, lytic functional capacity. Collectively, the data indicate that E. purpurea, at least, and possibly other plant compounds, appear to contain phytochemicals capable of stimulating de novo production of NK cells, as well as augmenting their cytolytic function, in animals of advanced age.

Aging↗
PubMed2002

GC-MS analysis of the lipophilic principles of Echinacea purpurea and evaluation of cucumber mosaic cucumovirus infection.

An analytical GC-MS method based on nonpolar fused silica capillary column was developed to analyze the lipophilic constituents, mainly alkamides, from the root extracts of Echinacea purpurea (L.) Moench. In particular, the proposed method was applied to evaluate the phytochemical impacts of cucumber mosaic cucumovirus (CMV) infection on the plant's lipophilic marker phytochemicals. Methanolic (70% v/v) extracts, obtained from root materials by ultrasonic treatments, were subjected to liquid-liquid extraction with n-hexane-ethyl acetate (1:1 v/v) to recover the lipophilic, volatile to semivolatile, principles. Seventeen components, including the 11 alkamides known to E. purpurea roots, were identified in the GC-MS traces of the analyzed fractions and efficiently separated in a turnaround time of 25 min. CMV infection was found to be responsible for significant variations in the relative compositions of the major constituents, in particular germacrene D, Dodeca-2E, 4E, 8Z, 10Z(E)-tetraenoic acid isobutylamide cis/trans isomers, Undeca-2Z, 4E-diene-8, 10-diynoic acid isobutylamide and Dodeca-2E, 4Z-diene-8, 10-diynoic acid isobutylamide.

Cucumovirus↗
PubMed2003

Trace elements analysis of Echinacea purpurea--herbal medicinal.

Elemental composition of Echinacea purpurea (Asteracae), grown in Serbia under strongly controlled conditions, has been studied. To distinguish elemental patterns of different parts of the plant, the content of Zn, Fe, Cu, Mn, Ca, Mg, Sr, Ni, and Li in root versus upper plant parts were determined, by flame atomic absorption and flame atomic emission spectrometry. Analyses of the mentioned elements in soil and in an ethanolic extract of E. purpurea were made, too. The trace element data were evaluated by multivariate methods, i.e. principal component analysis and hierarchical cluster analysis. This revealed two groups of elements (I: Fe, Cu, Mn, Li; II: Ca, Mg, Zn, Ni), while trace element profiles of root, stem, leaves, and flowers of this plant differed significantly. However, no significant difference in the trace element patterns between the summer and the autumn harvest samples was found.

Echinacea↗
PubMed2003

Modulation of apoptosis in mice treated with Echinacea and St. John's wort.

Apoptosis, or programmed cell death (PCD), is a physiological active cellular suicide process that occurs in non-contiguous cells, and is usually not associated with inflammation. The apoptotic process can be modulated by various stimuli, including hormones, cytokines, growth factors, and some chemotherapeutic agents. To determine whether Echinacea purpurea and Hypericum perforatum are able to regulate the process of apoptosis in vivo and to define the role of the Fas-Ag and Bcl-2 signal transduction cascade, we have orally treated groups of mice with these vegetable drugs for 14 days. The splenic lymphocytes from mice treated with E. purpurea and H. perforatum at the two dose levels used (30 and 100 mg kg(-1) per day) were shown to be significantly more resistant to apoptosis than those from mice treated only with the vehicle. In addition, mice treated with the natural substances showed a decrease in Fas-Ag expression and an increase in Bcl-2 expression. In conclusion, our results shown that in vivo the studied drugs modulate apoptosis in mice splenic lymphocytes and that this action could be mediated in part by a decrease in Fas-Ag expression and in part by an increase in Bcl-2 expression.

Animals↗
PubMed2000

Retention of caffeic acid derivatives in dried Echinacea purpurea.

Different drying methods were applied to fresh Canadian-grown Echinacea purpurea flowers to determine optimal drying procedures for preserving caffeic acid derivatives. Fresh flowers of E. purpurea were dried by freeze-drying (FD), vacuum microwave drying with full vacuum (VMD), and air-drying (AD) at 25, 40, and 70 degrees C. Using HPLC, chicoric acid and caftaric acid levels were quantitated in dried flowers. These acids were significantly affected by the drying method conditions used. Although significant (p < 0.05) loss of chicoric acid was observed when flowers were stored at high moisture, VMD flowers with a low moisture content retained the highest levels of chicoric acid and caftaric acid similar to FD flowers. Flowers that were AD at 25 degrees C retained about 50%, while those dried by AD at 70 degrees C resulted in the lowest retention of these acids. Although flowers dried by AD at 40 degrees C retained relatively high amounts of chicoric acid and caftaric acid, the time (55 h) required to reach optimal drying was considerably longer than that (47 min) for VMD.

Caffeic Acids↗
PubMed2000

Retention of alkamides in dried Echinacea purpurea.

Different drying methods, such as freeze-drying (FD), vacuum microwave drying (VMD), and air-drying (AD), were applied to fresh roots and leaves of Canadian-grown Echinacea purpurea to determine the optimal method for preserving alkamide levels. Using HPLC, six alkamide fractions (alkamides 1, 2, 3, 6a/6, 7, 8/9) were quantitated in dried roots, whereas four alkamide fractions (alkamides 1, 2, 3, 8/9) were measured in dried leaves. Different elution conditions used in HPLC for alkamide analysis did not affect the eluted fractions nor the quantitation of different alkamides. Individual alkamide concentrations in roots and leaves were affected by the drying methods used. To preserve higher levels of total alkamides, FD was found to be the best method, VMD was a superior method for drying roots than AD at 70 degrees C, while AD at 50 degrees C was the preferred method for drying leaves of E. purpurea.

Amides↗
PubMed2001

Echinacea standardization: analytical methods for phenolic compounds and typical levels in medicinal species.

A proposed standard extraction and HPLC analysis method has been used to measure typical levels of various phenolic compounds in the medicinally used Echinacea species. Chicoric acid was the main phenolic in E. purpurea roots (mean 2.27% summer, 1.68% autumn) and tops (2.02% summer, 0.52% autumn), and echinacoside was the main phenolic in E. angustifolia (1.04%) and E. pallida roots (0.34%). Caftaric acid was the other main phenolic compound in E. purpurea roots (0.40% summer, 0.35% autumn) and tops (0.82% summer, 0.18% autumn), and cynarin was a characteristic component of E. angustifolia roots (0.12%). Enzymatic browning during extraction could reduce the measured levels of phenolic compounds by >50%. Colorimetric analyses for total phenolics correlated well with the HPLC results for E. purpurea and E. angustifolia, but the colorimetric method gave higher values.

Chromatography, High Pressure Liquid↗
PubMed2003

HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products.

A reversed-phase high-performance liquid chromatography (HPLC) method has been developed to determine caffeic acid derivatives, for example, cichoric acid, and alkamides in plant parts and herbal products of Echinacea purpurea. The method consists of an extraction procedure whereby the hydrophilic phenolics as well as the lipophilic alkamides are released from the samples, followed by the analytical HPLC procedure for quantitative determination of these compounds. The method is the first one validated for the determination of these two groups of compounds in the same procedure. Naringenin has been used as an internal standard, as no other flavanones are present in the extract and it does not interfere with any of the compounds under investigation. Analysis of Danish-grown plant material shows that it is possible to raise plants of a very high chemical quality in Denmark. A selection of international herbal products available on the Danish market show surprisingly variable quality, not necessarily reflecting the product information given on the labels.

Amides↗
PubMed2005

Human gene expression as a tool to determine horticultural maturity in a bioactive plant (Echinacea purpurea L. Moench).

A phenological study was conducted to determine the impact of harvest maturity on the immune-modulating properties of Echinacea purpurea. The aerial parts of this plant were collected during seven stages of development and were assayed for a common botanical marker for this species, cichoric acid. Plants of selected development stages were also assayed for total polysaccharides and compared for their immune-modulating effects on the THP-1 monocyte/macrophage cell line by means of a gene expression study. Although the concentration of cichoric acid did not change significantly during the course of the study, stage 1 (advanced vegetative) had the highest concentration of total polysaccharides and exhibited the most potent induction activity on immune-modulating cytokines such as interferon-gamma and tumor necrosis factor-alpha. These findings suggest that the use of gene expression may be an effective tool not only to standardize botanical extracts but also to optimize harvest time.

Biomarkers↗
PubMed2006

Caffeic acid derivatives production by hairy root cultures of Echinacea purpurea.

Inoculation of leaf explants of Echinacea purpurea (Moench) with Agrobacterium rhizogenes induced hairy roots with the capacity to produce biologically active caffeic acid derivatives (CADs), especially cichoric acid. The kinetics of growth, the uptake of macronutrients, and the accumulation of CADs were investigated in heterotrophically cultured hairy roots for a 50 day period. A maximum of 12.2 g L(-1) dry biomass was achieved in MS nutrients supplemented with 30 g L(-1) sucrose on day 40. The mathematical relationship between hairy root growth and conductivity was established during the exponential phase in Erlenmeyer flasks. HPLC analyses of methanolic (0.1% phosphoric acid; 70:30, v/v) extracts from hairy roots revealed the presence of important CADs: cichoric acid (19.21 mg g(-1) dry biomass), caftaric acid (3.56 mg g(-1) dry biomass), and chlorogenic acid (0.93 mg g(-1) dry biomass). These results demonstrate that biotechnological production of CADs in hairy roots of E. purpurea is possible. Furthermore, these hairy root cultures offer, for the very first time, an excellent biological model to study the biosynthetic pathway of medicinally important CADs.

Butylamines↗